5-([(Z)-Methoxyimino]{2-[(2-methylphenoxy)methyl]phenyl}methyl)-1,3,4-oxadiazole-2(3H)-thione dimethyl sulfoxide monosolvate

The title compound crystallizes in the monoclinic space group P21 /c with one molecule in the asymmetric unit. In the crystal, (9) chains of C—H⋯O interactions are formed, propogating in the c-axis direction. The N—H hydrogen atom forms a strong hydrogen bond with the oxygen atom of a DMSO solvate molecule.


Structure description
The newly synthesized title compound C 2 H 6 OSÁC 18 H 17 N 3 O 3 S (1, Fig. 1) is derived from Kresoxim methyl fungicide and is a member of the strobilurin family. The broad spectrum nature of 1 allows it to have site-specific action and high efficacy against fungal diseases (Anke et al.1977;Olaya et al. 1998;Patel et al., 2012;Esteve-Turrillas et al., 2011;Mercader et al., 2008;Balba, 2007;Cash & Cronan, 2001, Ammermann et al., 2000Balba, 2007;Kant et al., 2012). The metabolites of compounds such as 1 are easily translocated in nature. The modified structure of 1 has various antifungal, antibacterial and anticancer properties; however, tracing out the exact mode of action of this type of compound will require further study of its bio-efficacy.
Compound 1 crystallizes in the monoclinic space group P2 1 /c with one strobilurin molecule and one solvent molecule in the asymmetric unit. It consists of a toluene ring linked via a methoxy group to a phenyl ring, which is then linked to a five-membered 1,3,4 oxadiazole-2-thione ring. The carbon atom linking the five-membered ring to the phenyl ring additionally has a methoxyamino substituent branching off from it.
In the crystal of 1, the solvent DMSO molecule accepts both an N-HÁ Á ÁO hydrogen bond with the five-membered ring and a weak C-HÁ Á ÁO interaction with an adjacent data reports DMSO molecule (symmetry operation: x, 3 2 À y, À 1 2 + z) (Fig. 2, Table 1). Additionally, the methoxyamino substituent forms a weak C-HÁ Á ÁO interaction with the methoxy group in an adjacent molecule (symmetry operation: x, 1 2 À y, 1 2 + z), forming a C 1 1 (9) chain propogating in the c-axis direction. A pseudopolymorph of this structure has also be determined with water as solvent (Shripanavar et al., 2023)

Synthesis and crystallization
The Kresoxim methyl hydrazone compound (3.13 g, 0.01 mol) was dissolved in a solution of KOH (0.01 mol) in water (20 ml) and CS 2 (0.01 mol) in ethanol (20 ml) and then the mixture was refluxed for 8 h. After the reaction was complete, the mixture was cooled at room temperature and neutralized with diluted HCl (4 N). The precipitated product was filtered and washed with water to dry it. Crystals were obtained by evaporation of a DMSO solution.

Refinement
Crystal data, data collection and structure refinement details for the structure are summarized in Table 2.
Antibiot. 30, 806-810.  Diagram showing the packing of 1 with hydrogen bonds shown as dashed lines. The molecules of 1 are linked by C-HÁ Á ÁO interactions forming a C 1 1 (9) chain propagating in the c-axis direction. Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) x; Ày þ 1 2 ; z þ 1 2 ; (ii) x; Ày þ 3 2 ; z À 1 2 .  Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. A riding model was used for the H atoms attached to C with atomic displacement parameters = 1.2U eq (C) [1.5U eq (C) for methyl groups] while the N-H hydrogen atom was refined isotropically.